West Queen West, as locals have dubbed it, is the lesser-explored stretch of Toronto's main shopping thoroughfare. It remains relatively spared from mega-chain stores while catering to a gayer, art-savvier population.

Start your day at the Gladstone Hotel (GladstoneHotel.com), a historic landmark and cultural center where you can enjoy a spot of tea — with a scone — while browsing cutting-edge installations on the upper floors.

More eye candy awaits as you head east toward Ossington Avenue. Check out the nearby Twist Gallery (TwistGallery.ca) — a 5,000-square-foot converted loft space with arched windows and exposed wooden beams — showcasing noteworthy local photographers and art events. Down a few blocks, the Stephen Bulger Gallery (BulgerGallery.com) is one of the most respected photography showrooms in the country. Recent exhibits have included works by Joel Meyerowitz and Vivian Maier, and Bulger also hosts free film screenings every Saturday in their 50-seat projection room and bar, Camera.

For some retail therapy, start with In Abstracto (InAbstracto.wordpress.com), a lesbian-run design store with a selection of mid-century furniture and jewelry by independent artisans. Style Garage (StyleGarage.com) has industrial-chic homeware displayed throughout its two levels, and ships anything worldwide, from custom upholstery and factory chairs to lush sectionals by local interiors brand Gus Modern.

Bookworms unite at the diminutive Weekend Variety, an indie books-and-art shop owned by a former New York publisher. The dollhouse-like space has curated reads, collectible prints, and highly giftable stationery. Look out for the Queer Scout stickers and Toronto-based illustrator Stephanie Cheng’s hilarious “Hotline Bling”–inspired pins.

Splurge on some made-in-Toronto menswear at Annie Aime (Shop.AnnieAime.com), which stocks Outclass and Kovalum, two labels nearly impossible to find stateside, then raid the racks at IMissYou for secondhand designer steals and vintage accessories. Around the corner, GravityPope (GravityPope.com) is known as the most sophisticated shoe store in Toronto. It’s tastefully furnished with Louis XVI–style commodes, rococo chandeliers, and a stunning glass-and-brass 1930s Deco staircase, all sourced from an old movie theater in Buenos Aires.

For lunch, head across the avenue to Union (Union72.ca), a new and noteworthy farm-to-table bistro with a beer garden. Discerning diners should hit up veggie-centric Dandylion (RestaurantDandylion.com), where veteran chef Jay Carter serves modern French cuisine. The tiny open-brick space, which was entirely refurbished by Carter and his father to accommodate just 30 seats, ranks sixth in this year’s coveted Canada’s 100 Best Restaurants.

West Queen West is also a booming nightlife hub. Hole-in-the-wall LGBT resto-bar TheBeaver (TheBeaverToronto.com) has DJ sets, dress-up karaoke, and irreverent Friday theme nights like “Puppy Love” geared toward twinks and their daddies. TheDrake (TheDrakeHotel.ca), a boutique hotel (no relation to the T-dot-born rapper), houses a concert venue in its basement, the Drake Underground. Before heading home, stop by its adjacent concept store (DrakeGeneralStore.ca) — the best spot to pick up last-minute quirky Canadian memorabilia such as Blue Jays baseball shirts (written in Japanese) and Yukon-themed dinnerware.

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